Mass spectrometry of Sauroxine, a Lycopodium alkaloid with AChE inhibitory activity

CIFUENTE D; M VALLEJO; ORTEGA M,; CABRERA J,; TONN C; AGNESE A.M.,; ARDANAZ C

Khartoum

Simposio; 15th symposium of the Natural Products Chemistry Research Network for Eastern and Central Africa (NAPRECA); 2013

During recent years, Lycopodium alkaloids have gained great interest due to their important pharmacological properties as wellas for their complex molecular architectures. Un important series of Lycopodium alkaloids isolated from Huperzia saururus(Lam.) Trevis have been reported possessing important medicinal effects which can act either as potent inhibitors ofacetylcholinesterase (AChE) and/or on memory-related phenomena.H. saururus (Lam.) Trevis. (Lycopodiaceae) ("cola de quirquincho", "piyiyay" or "piyijay") is a native Argentine species used inthe ethnomedicine as aphrodisiac and memory improver. Its habitat spreads from the northwest region of the country to thesierras of the center (Cordoba) and south of Buenos Aires.In previous investigations ten alkaloids were isolated from H. saururus. Also it was demonstrated by us that sauroine, the mainalkaloid present in the species, strongly enhances hippocampal Long Term Potentiation (LTP) as well as memory retentiondemonstrated in vivo. At the same time it was not an inhibitor of the acetylcholinesterase enzyme. On contrary, sauroxine (othermajority alkaloid) was an acetylcholinesterase inhibitor but had no effect on LTP.In the present work, using quadrupole ion trap (QIT)-MS instrument, we report and discuss the gas chromatography/electronionization mass spectrometry (GC/EIMS)(low resolution) and collision-induced dissociation tandemmass spectrometry (CIDMS/MS) fragmentation of sauroxine (MS in time) a Likopodium alkaloids isolated from Huperziasaururus (Lam.) Trevi. Themass spectrometry studies presented in this rationale has been very useful to support the structural determinationof sauroxine andLikopodium alkaloids analoges.